


Cowboys with Benefits

by MALLR4TS



Category: Red Dead Redemption (Video Games)
Genre: Cunnilingus, F/M, Flirting, Fluff, Fluff and Smut, Friends With Benefits, Friends to Lovers, Orgasm, Sex, Smut, Unfinished, Vaginal Fingering, Vaginal Sex, handjobs, ongoing work
Language: English
Status: In-Progress
Published: 2019-08-31
Updated: 2020-07-15
Packaged: 2020-10-04 08:18:02
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 3,577
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20467919
Author URL: https://archiveofourown.org/users/MALLR4TS/pseuds/MALLR4TS
Summary: Your constant flirting with Bill finally paid off as the two of you form a friends with benefits attachment.Ongoing work!!





	1. Chapter 1

**Author's Note:**

> First chapter. Feel free to suggest/request future chapters. I dont have much planned for this series, just basically adding all my Bill fics to here :^)
> 
> My Twitter and Tumblr are @MALLR4TS

**Notes for the Chapter:**

> EDIT: [11/08/20] Fixed some grammar n spelling

You're not quite sure how it happened. Well, you do, but the words kinda slipped out of your mouth. 

You always teasingly flirted with Bill around camp, but only because he was always so flustered around you. It started with small comments, calling him names like 'big boy' and 'handsome.' You could tell Bill enjoyed these small comments. You'd neatly tuck these names into passing comments, like the time you gave him some coffee and said:  
"This is for you, handsome."  
Or whenever you'd catch him drinking, you'd walk past and say:  
"Having fun there, big boy?" 

You could tell it drove him crazy. You're not sure if that was from genuine lack of female attention, or if he was genuinely interested in you. At first, you did it just to be a tease, like you were to the rest of the camp, but then you really started thinking into it.

Bill was a big guy. As in, his structure. You'd find your mind wandering off, thinking about if the rest of him is really that big. Or what it's like to be held in those strong arms. Or how it'd feel to have his rugged beard brushing against you. Or how long he could hold you up for against a tree as he plowed into you. 

So then the small comments became full-on flirtatious sentences. You never planned on making the first move, you hoped he would, but whenever you flirted with him he'd always fluster and stutter a response. He flirted back when he managed to finally string a sentence together.

You saw him cleaning his gun once, and commented on it:  
"You're doing a good job at cleaning that gun there, Bill," you said as you wandered over to him. You stood behind him and lent forward, peering over his shoulder as your hands held onto his shoulders. "You really know how to rub in that gun oil," you began to trace one of your hands up and down his arm, teasingly. "It makes me wonder what else you can do with those big hands of yours, Mr. Williamson," you sighed.  
You felt him tense up under your touch, he looked back up at you over his shoulder.  
"You.. you do?" Bill asked, nervously.  
"Oh, of course, I do," you replied as you moved your position to stand next to him, leaning back on the table, looking down at where he was sat.  
"Well, I guess I'd like to show you sometime.. if you'd let me," Bill replied, somewhat quietly. It was as if he didn't want anyone else in the camp to hear. Which was understandable, as they'd tease him for it.  
"You always know where my tent is, big boy," you said as you lent forward and ran your hand along his cheek, ruffling up his beard. "Goodbye for now," you walked off. You felt Bill lean his head more against your hand as it began to leave his face, craving more of your touch.  
You overheard him grumble as you walked off, annoyed he wasn't getting more of you right now. 

Later that night you happened to be put on guard duty. No bother. There were many chances to lie in bed hoping Bill would wander into your tent.  
You did your usual rounds of walking around the forest of Horseshoe Overlook, circling the camp. It was 2 am, you finished at 4 am.  
You always took notice of where everyone was. Who was asleep, who was up drinking, who wasn't at the camp, etc. What you hadn't noticed was Bill. Where was he? Who knows? Not you.

Until you heard a rustle in the distance. You began slowly creeping over. It was a fair bit from camp, 10 meters or so from the horses. You eventually could see the outline of someone's figure down behind a tree. You stood a few feet away, diagonally behind them.  
"Whos there?" You half-shouted, your shotgun in your hands.  
"Awh shit!" You heard them say. It was Bill.  
"Bill?" You asked him.  
"Fuck. Uhh, nows not a good time!" He replied slightly too late as you had already stepped a bit closer and could see his hands down his pants.  
"Oh shit!" You said as you stepped backward, turning away. "Oh gosh, I'm so sorry, Bill. I didn't mean to disturb you. I didn't know who you were!"  
You could hear him quickly buckling up his jeans and belt.  
"Its uhh.. it's okay. I probably should have warned you.. I guess,"  
"Well, I guess you should have. I could have blown your head off," you replied. 

There was a long pause. 

"So do you need a hand with that?" You asked him. Oops. That thought wasn't meant to slip out.  
"With.. with what? My.. uh.." Bill replied. You turned around to face him.  
"With that cock of yours," you softly replied.  
"You uhh.. yeah," Bill mumbled.  
You walked over to him, resting the gun against the tree. You placed your hands on his knees as you knelt down in between them, facing him.  
"You seem nervous," you teased.  
"I just, never thought this would actually happen."  
"Bill, I've been flirtin' with you since I met you. I was waiting for it to happen," you smiled.  
"I kno' and I've been tryna flirt back, just don't really kno' what to say," he replied. You could hear the frustration in his voice.  
"It's okay, big boy. I'm here now," you cooed as you reached forward and rubbed your hand over his bulge. You heard him breathe sharply as he watched.  
"Been waiting for this for a long time?" You asked him. He nodded, not breaking eye contact with your hand rubbing over him.  
"How long?" You ask.  
"Since we met," he replied.  
"Awh, that's real sweet," you said as you began unbuckling his belt and pulling his pants down slightly. 

His cock sprung out, excited to see you. You had a good imagination, as you had pictured it to be just as big as it actually was. It wasn't too long in length, about average, but it was so thick. His breath hitched, and you felt his cock twitch as you held it for the first time. You could feel how hard he was as you slowly began pumping your hand up and down it, feeling his veins press against the palm of your hand. 

"So tell me, what were you thinkin' about earlier?" You asked.  
"You mean when I was.. doin' what yer doin' now?" he asked, looking up at you.  
"Mhmm," you said as you nodded. Bill paused.  
"You," he sheepishly replied.  
"What exactly about me?" You asked him as you picked up the pace a little, and lent in to start kissing from his cheek down to his neck. He lent his head over slightly, very much welcoming your touch.  
"Just you, yanno," he sighed.  
"I don't know, Bill. I'd love for you to explain to me," you teased as you nipped against his skin.  
"Uh.. me and you, fuckin', stuff like that," he replied.  
"You know I'd love to do that, very much, Mr. Williamson," you whispered into his ear.  
"God. Please. Lemme fuck you right now," he begged.  
"Not yet. Gotta keep you waitin' a bit."  
"You tease me too much," he sulked.  
"Oh you love it, I know you do," you replied as you pumped faster. It caught him off guard, and you could tell from the way he sucked his breath in and let out a deep sigh. 

You continued to kiss his neck, along his jawline, enjoying the way his rough hair rubbed against you. You peeked up to see his eyes were shut, head leaning back against the tree, mouth slightly parted. He reached one arm forward to hold your waist, kneading at the fabric. 

"Please, lemme kiss ya'," he asked politely.  
"You don't need to ask me," you purred.  
"Felt it'd be rude not to," he said as his other hand came up to cup your cheek. He wasted no time leaning forward to finally meet his lips with yours. Softly kissing you at first, getting used to the feeling of your mouth pressed against his. Your strokes had slowed down, focusing on the kiss, and eventually, you picked them back up again.  
This caught Bill off guard, he let out a moan then kissed you deeper, harder, pulling you against him so your legs sat either side of his. You could feel his hips moving as if he was trying to buck up into your hand, though your weight kept him firm on the ground. 

"Yer doin' so good.. I.. yer makin' me see stars here, (Y/N)."  
"Good," you smiled as you kissed his cheek. You looked down and focused on your hand pumping away at his cock, going fast but not to the point where you were losing rhythm.  
"You look so good, Bill. I love the sight of you coming undone," you purred.  
"What's that mean?" he asked through moans.  
"It means you look hot when you're all flustered. It makes me wet. I can't wait to be fucking your cock."  
"Oh.. oh god," Bill moaned, his eyes shutting.  
"Would you enjoy that, big boy? Would you enjoy me riding you? Or you taking me on all fours, plowing into me?" you ask as you lean in to kiss his neck again.  
"So much.. It's all I think about," Bill admitted.  
"Oh, that's very naughty of you, Mr. Williamson. But its okay, because I've been thinking about the exact same things. And more."  
"Please.. please tell me," he sighed. You smiled and laughed lightly.  
"Well, I've thought about many things. I'd love to wake up in the night to find you between my legs. I'm sure your beard would feel so nice rubbing against me."  
"Oh, (Y/N), just you wait," he purred. He tried again at bucking his hips up against your hand, begging for more friction.  
"And I'd love to feel your hands gripping my hips, holdin' me tight as you fuck that big cock of yours into my pussy."  
"Shit. (Y/N). Yer gonna make me cum," Bill sighed.  
"I hope I do. I want you to. I'd love for you to cum for me, big boy," you whispered against his ear. You picked up the pace, really pumping his big cock as you felt it tense and swell in your hand. 

"Are you gonna cum for me?" You ask.  
Bill nodded.  
"Go on then, handsome. I can't wait. I think I deserve it, I've worked your cock so well tonight," you kissed along his neck until you found a nice spot, and began lightly biting and sucking the skin. Bills breath hitched before letting out a string of deep moans.

Bill let out a long deeper sigh as he came, his head tilting back and lightly hitting the tree.  
"Fuck," he sighed. You slowed your hand down, really trying to milk his orgasm. You could feel his legs shaking underneath you. Bill leaned in to lightly kiss you as he finished off. He wasted no time in pulling a rag out of his pocket and cleaning the both of you off. He quickly zipped up his pants and pulled you fully on his lap, his arms tightly around your waist as he kissed you deeper. 

"I can't believe tha' just happened," Bill said against your lips as he pulled off slightly.  
"Believe it. And believe there'll be more, if you want," you replied.  
"Oh. Of course, I want there t' be more," he somewhat begged.  
"Well, I guess you'll just have to find yourself wandering into my tent often then," you teased. Bill purred as he buried his head into your neck, his hat brushing against your cheek.  
"Come on, you," you said as you began to stand up, making Bill whine. "I need to get back on duty."  
You offered Bill a hand and helped him up. The two of you made your way slowly back into camp. 

Bills hand snuck over and found itself very comfortably in yours. The size of his hands wrapping around your much smaller ones. The two of you didn't talk much, preferring to enjoy each other's silent company. 

"Can I stay yours tonight?" he asked.  
"You can stay any night," you replied. Bill smiled.  
"I'm gunna bring my roll in yer tent to keep us warmer. When do you finish guard duty?"  
"4," you said as you looked at your watch. "Hour and a half left."  
"Well, I guess I'll see you then," you purred at him, leaning into him. "Keep the bed warm for me."  
"Course I will," he said as he leaned down to give you a small kiss, worried someone was awake and would see the two of you.  
"That's my big boy, now go on, shoo," you smiled as you let go of him. Bill smiled back and headed off into the camp. You turned on your heel and went back on duty, already beginning to count down the minutes. 

4am. 

You gently wake up Lenny for his turn on duty. He's always so polite, asking you how it was, how you were, etc. You handed over the shotgun then made your way over to your tent.  
Bill was asleep, what a surprise. He had pushed both of your bedrolls together to somewhat make a double bed. He lay on his side, both your blankets on top of him with more than enough space for you to squeeze in.  
You undressed to lighter clothing and tucked yourself in, rolling onto your side to snuggle up against Bill. He didn't wake, but he could sense you were there. His arm snuck around your waist as he buried his head down against the top of your head.  
Your eyes were already heavy, and before you knew it you were asleep. Safe and sound.


	2. Chapter 2

At first, you thought you were having a wet dream. You stirred in your sleep, aroused, letting out a soft moan as you slowly woke up. You quickly realized that Bill was spooning you, his hand reaching around and into your undergarments. His thick fingers were rubbing nicely over your clit, in quick circular motions. You moaned again, instinctively pushing your ass back to grind against his semi-hard cock.   
"Yer awake," Bill grumbled from behind you, pressing slightly harder against your clit.   
"Good morning, big boy," you half spoke, half sighed. Bill softly growled.  
"You know damn well how much I like bein' called that."   
"That's why I call it you," you replied with another grind against his crotch.   
"And you know damn well what it makes me wanna do to you," Bill replied and without warning, slid one of his thick fingers knuckle-deep inside you. You snapped out of your groggy, half-asleep phase thanks to the help of Bill, letting out a loud moan, loud enough to let anyone nearby know what was happening.   
"Yer tighter than I ever imagined," he muttered against you, focusing on pumping his thick finger in and out of you.   
You continued to grind your ass against his now fully hard cock. Bill repositioned his finger and rutted it in you, hitting that sweet spot which caused you to let out a yelp. His other hand quickly came to cover your mouth, hushing you.   
"You wanna wake everyone up?"  
"Hm? What time is it?"   
"Early. I ain't had my breakfast, and I'm pretty hungry." 

Bill rolled on top of you, pinning you down as he began hungrily kissing your neck, nipping and licking at your skin. You moaned again as his finger slid back inside of you, quickly joined with another equally thick finger.  
"You takin' revenge on me? Teasin' me as much as I tease you?" you ask him.   
"All I'm doin' here is teasin' myself. I'll just have to tease you in future, I'm too impatient right now." And with that, Bill pulled off your undergarments, leaving them over one of your ankles as he quickly went to spreading your legs apart and having a look. You shuffle up and slid your top off, throwing it to the side of your tent.   
The tents thick canvas blocked out a large chunk of the light, but Bill could still see you well enough to admire your figure.   
He brushed his hands down your body, over the curves of your hips, the dip of your waist, the smoothness of your legs.   
"Better than art," was all he could stutter out as he blushed at the sight of you.   
"You're too kind, Mr. Williamson," you replied.  
"I ain't kind keepin' you waitin' like this," Bill said as he shuffled down the rollmat and lay down on his front, holding both your thighs firmly in his bear-size hands as he kissed them. 

You could tell Bill was trying his hardest to be somewhat sexy. Taking his time to kiss along your thighs, slowing down as he neared your pussy, then stopping and moving over to the other thigh. His beard brushed over you, lightly in some areas, but most of it was rough and scratchy against your soft skin. It was a nice feeling, the roughness mixing with his soft small kisses. You kept your head rolled back, impatiently waiting. You deserved to be teased, considering how much you'd done to Bill. You deserved it.   
And then he gave in, letting his tongue flatten out and lick slowly up your pussy. You let out a soft, quiet sigh. Bill did it again, another long slow lick across your cunt. 

"You're so sweet," he complimented. You were about to thank him but let out a sharp moan as he began sucking on your clit. Every so often Bill would flatten his tongue and brush it over you, flicking it in a circle over your clit, enjoying the sounds you made despite attempting to be quiet.   
Bills grip on your thighs tightened as he pushed them up more, your knees almost reaching your shoulders. He let go of one, moving his hand slowly down your thigh before sliding a thigh finger back inside of you, his tongue playing with your clit. 

You let out a moan that anybody nearby definitely heard. 

"Billll," you sighed, reaching down to rest your hand on his head.   
"Mhmm?" he hummed against your clit, building up a pace as he pumped his finger in and out of you.  
"More, please," you asked nicely.

Bill accepted your request, sliding another thick finger into you. You let out a relieved moan, panting softly as Bill continued to run his tongue back and forth. Bills fingers picked up the pace, curling slightly to rub over that spot inside of you. 

"God, I'd love to fuck you right now," Bill said against your pussy, his beard brushing over you.  
"Why don't you?" you ask.  
"Gotta keep you waitin'. You did the same to me."  
You laughed lightly, but your laugher turned into moans as Bill went back to eating you out. 

You let out a very sudden and sharp moan as Bill managed to find your G spot, your body starting to tingle.  
"There it is," he mumbled against you.   
Bill continued to rub against it, his fingers fucking hard into you. Your legs instinctively tried to close but Bill kept them spread, his hand gripping tightly on your thigh as he pushed it down towards the floor.   
You started to shudder, feeling your orgasm building up. Bill continued playing with your clit, devouring it with his mouth. You eventually couldn't take the pleasure anymore and came hard, your whole body shaking. One of your hands gripped Bill whilst the other covered your mouth, trying not to be quiet. 

Bills fingers slowed down slightly but his mouth didn't stop, milking you as much as he could. As you calmed down, he stopped. 

Bill pulled his fingers out and sat upright, wiping them on his jeans then wiping his face with his shirt sleeve. Lovely.   
You propped yourself up on your elbows, still breathing heavily. 

"Good?" Bill asked you. All you could do was nod in response, your mouth parted slightly as you calmed your breathing.  
"I'm gonna go get us some coffee. Come out when you're ready," Bill said as he lent over you and kissed you. All you could taste was yourself on his lips, his beard still slightly damp against your skin. 

Bill broke the kiss and got up. He left your tent, making sure the tent flaps shut behind him. You took your time cleaning yourself up, getting dressed, and eventually leaving your tent also, rolling the flaps open to let some air in.

Bill was sat over on the table, drinking a cup of coffee rather than a beer for once. Your cup was next to him, along with an empty seat for you. You wandered over and without thinking, kissed his cheek before sitting down at the table. 

The two of you realized what you'd done very quickly, forgetting that you were trying to keep your thing a secret. Only a few camp members were up and hopefully, none of them saw. You sipped at your coffee nervously but calmed down as you felt Bill's hand rest on your knee. You gave him a smile.

"Enjoy your breakfast?" you jokingly asked him.   
"It was delicious," he grinned. You couldn't help but laugh.  
"Same thing tomorrow?"   
"Mhmm," he grinned.


End file.
